Him, an adventurer, CISO, soldier, Marine, law officer, author, professor, spy, yachty, motorcyclist, photographer. Her, was the church lady librarian, got divorced, joined a motorcycle gang, became a hacker, and world adventurer.

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New jobs and lifestyle changes

In November of 2017 my former agency leadership decided to go with a career intelligence community professional to lead a cyber program rather than the cyber guy (me!). This isn’t necessarily a bad choice but it put me in a bind because I had been leading the program for nearly a year and had exceeded measures of performance and effectiveness in the double digit range. Having run the program and having somebody else come in to run the program is nothing new in government. That isn’t fun but not unusual. My leadership positioned the transition as a promotion and growth opportunity. The replacement was still a GS15 and I couldn’t report to a subordinate level, and he was a former direct report which makes things all kinds of squishy.

So, I took my medicine was promoted to the Deputy Under Secretary of Intelligence Operations Staff, added counter terrorism to my duties, and commenced working on PPD21 (critical infrastructure) intelligence needs along with anything else my boss asked. If I could say anything about my bosses at I&A it was that I had some excellent leadership. Yet I started looking for a job shift. I was good at intelligence work, I had fun, but I am not an intelligence officer. I posted my article the million dollar CISO and the calls started to flood in. I had some naysayers in the community that said I was arrogant or was not going to get what I was looking for… But, yet I persisted.

Your critics sharpen your blade.

I had a few people who said I was sounding trashy or not comporting myself with the appropriate level of aplomb. In some ways they were saying I was old and should act old. In a few cases they were like you are this titan you shouldn’t even discuss looking for a job as it made me look weak. Yes these critics were right and wrong and in some cases they gave me a bit to ponder, but I am me. I am an iconoclast and have traded for good and bad my reputation by being honest and often going against the way things are done. The end results have always been much more honest and less stressful in the long term.

For some context. I had taken the “yes” vow back in January 2017. I had worked diligently to listen to anybody and everybody and be open to just about anything.

I got a call from a recruiter. The recruiter said, “Hey would you talk to this financial corporation about becoming the VP and CISO?” I talked to the recruiter, I talked to the director of operations, I talked to the head of incident response, I even talked to the COO. This is a blind call. They never disclosed who they were though it didn’t take a genius to figure it out. Near the end they said, “Hey what do you think about moving to Chicago?” I looked at the phone and said, “I’m not that excited. I’ve lived in the area before.” That was the end of the interview cycle. The recruiter called me up and said, “You do know the job was for $1.5 million a year?” No… No, I didn’t know that.

A company calls me up and says lets interview you. Four interviews going up the chain of command and I keep getting the queasy feeling. I feel they really want to abuse my rolodex and that the job is less about me being an expert and more about me being a sales conduit. The salary though is well north of $500K a year. The balance is between super cool technology and solutions and selling products to the government. I really hate sales.

A few government agencies called me, and I had one really sweet gig that I was hoping would come to fruition. I really wanted to stay in government and if possible the intelligence community. This one agency was my hottest prospect. They said they wanted me. We kept going around and around with paperwork. I submitted stuff to them. They ignored me for weeks. After three months I was finally getting tired. No start date, interminable challenges, and all kinds of stuff in the way. I didn’t even have a contingent job offer. All for a lateral transfer with no more money and lots more responsibility. My desire to stay in service to the nation was cooling rapidly.

Then I got a call, but not from the government.

A contact hits me up on Linked In and says he wants to talk to me about a company. He discusses the company in detail and is very humble about his ask. Would I talk about a job possibly with his boss a VP.

So, I told the contact, “Sure, I’ll talk to him, but you know I am seriously looking.” I spent almost 3 hours on the phone with the contact. This guy was somebody I could learn a lot from and maybe I might be able to give back a little bit. I spent an hour on the phone with the VP. He said come on down to their location. I said talk to me in a few weeks.
Then they closed the government.
It seems the only thing the government has gotten really good at is furloughing people. Come work for government for the low wages and stay for the furloughs. I called up (ok texted) the VP and said I suddenly find my calendar very open and could we make things happen. I was going to jump on my motorcycle, in my car, or buy my own ticket to the location. Instead plane tickets, car rentals, and a 16 hour (not really fudging that) a day for two-days itinerary shows up. I don’t know if they even understand what they are doing or if how they are doing it is kind of cool.

Long story short. I did an interview for two days. I took the job.

Now my experience as a senior leader candidate might be different from a standard interview but it is a long interview. All of that because they are looking for a cultural, technical, and capability fit within the current team. Who better to talk to than everybody? Some of the people were very positive. Some of the people were pretty negative. The interviewers were open and hoped I was interviewing them too. I was. The interviews are intense.

No, not stump the chump intense. They basically do a 360 review in two days. You talk to your future boss, and sometimes his boss. You talk to as many of your future peers as they can get into a room individually or as a group as they can find. They have you talk to people who would be your direct reports. They will even have you talk to people who will be your customer. They are all looking for people who will be a cultural fit. Do you have the people skills for an organization that puts people first? Do you have the technical skills to lead a team today and if necessary be a single contributor?

Whether they set out to do it they make their security talent go through this intense 360 review. The interview is about people skills, technology skills, and leadership skills. You might be talking about the select methods of analyzing a process injection in one breath and then how you handle inter-faith conflict between employees in a respectful way. The company raised half a million dollars for the victims of the Douglas shooting. In a day. When you leave the building you might see employee running groups. You might see Yoga classes. There are game rooms or ping pong tables scattered around the spaces.

Yeah, the money is good enough, but the culture is the reason I accepted the job. I find a distinct desire to do whatever it takes to make the company successful. There is positive intrinsic motivation to get things done. It deserves my best and I hope to give it. Work life balance they got it. Time to take care of the family do it. Focus on the things that make the company work? Every day because it is important.

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Cyber?

Cyber security and the technologies of securing the information enterprise of industry and government require a trans-disciplinary while still STEM focused research agenda. The term “cyber” itself denotes a human cognitive centric concept that deals with the disintermediation of technology centered within human activity. The changing focus from system threat mitigation to enterprise risk management has opened completely new areas of inquiry into security.